187401-45-2

Basic information

• Product Name: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-
• Synonyms: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-;5-chloro-6-isopropoxynicotinic acid
• CAS NO: 187401-45-2
• Molecular Formula: C₉H₁₀ClNO₃
• Molecular Weight: 215.635
• Mol File: 187401-45-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 314.9±37.0 °C(Predicted)
• Appearance: /
• Density: 1.310±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.55±0.10(Predicted)
• CAS DataBase Reference: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-(187401-45-2)
• EPA Substance Registry System: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-(187401-45-2)

Safety Data

• Hazardous Substances Data: 187401-45-2(Hazardous Substances Data)

Usage

General Description

The chemical compound, known as 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-, is an organic chemical characterized by its complex structure. It falls under the category of carbobicyclic compounds. The chemical is marked by the presence of a pyridine ring, (a six-membered ring containing five carbon atoms and one nitrogen atom), to which various functional groups are attached, including a carboxylic acid group (COOH) at the 3-position, a 5-chloro substituent, and a methylethoxy group at the 6-position. The compound is primarily used in the research and industrial sector as a specialty chemical. Its specific characteristics, such as reactivity and stability, are dependent upon its overall molecular structure.

Upstream product

• 41667-95-2 5,6-dichloronicotinic acid 
• 67-63-0 isopropyl alcohol 
• 187401-46-3 1-methylethyl 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylate 
• 54127-63-8 5-chloro-6-hydroxy-3-pyridinecarboxylic acid 

Downstream Products

• 1011476-57-5 5-chloro-6-isopropoxy-nicotinic acid (4-allyloxy-N-hydroxy-3,5-dimethyl-benzamidine) ester 
• 1011476-58-6 3-[3-(4-allyloxy-3,5-dimethyl-phenyl)-[1,2,4]oxadiazol-5-yl]-5-chloro-6-isopropoxy-pyridine 
• 1311202-93-3 tert butyl trans-3-[3-chloro-4-{5-(5-chloro-6-isopropoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl}phenoxy]cyclobutanecarboxylate 
• 1398512-07-6 C₂₄H₂₉ClN₄O₅ 
• 1398512-07-6 C₂₄H₂₉ClN₄O₅ 
• 1246389-12-7 tert-butyl 4-((5-chloro-4-(2-(5-chloro-6-isopropoxynicotinoyl)hydrazinecarbonyl)-2-fluorophenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1260021-72-4 5-[3-(3-bromo-2-ethylphenyl)-1,2,4-oxadiazol-5-yl]-3-chloro-2-[(1-methylethyl)oxy]pyridine 
• 1260021-61-1 5-[3-(3-bromo-2-chlorophenyl)-1,2,4-oxadiazol-5-yl]-3-chloro-2-[(1-methylethyl)oxy]pyridine 
• 1260021-48-4 5-[3-(3-bromo-2-methylphenyl)-1,2,4-oxadiazol-5-yl]-3-chloro-2-[(1-methylethyl)oxy]pyridine 
• 1260022-53-4 5-{3-[3-bromo-5-fluoro-2-(methyloxy)phenyl]-1,2,4-oxadiazol-5-yl}-3-chloro-2-[(1-methylethyl)oxy]pyridine 
• 1259032-15-9 ethyl 4-{7-[(Z)-{[({5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}carbonyl)oxy]imino}(amino)methyl]-1-[(4-methylphenyl)sulfonyl]-1H-indol-4-yl}butanoate 
• 1258959-73-7 ethyl 4-{7-[{[({3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)oxy]amino}(imino)methyl]-1-[(4-methylphenyl)sulfonyl]-1H-indol-4-yl}butanoate 
• 1258959-66-8 C₃₀H₃₁ClN₄O₇S 

Relevant articles and documents

Optimization of sphingosine-1-phosphate-1 receptor agonists: Effects of acidic, basic, and zwitterionic chemotypes on pharmacokinetic and pharmacodynamic profiles

The efficacy of the recently approved drug fingolimod (FTY720) in multiple sclerosis patients results from the action of its phosphate metabolite on sphingosine-1-phosphate S1P1 receptors, while a variety of side effects have been ascribed to its S1P3 receptor activity. Although S1P and phospho-fingolimod share the same structural elements of a zwitterionic headgroup and lipophilic tail, a variety of chemotypes have been found to show S1P1 receptor agonism. Here we describe a study of the tolerance of the S1P1 and S1P3 receptors toward bicyclic heterocycles of systematically varied shape and connectivity incorporating acidic, basic, or zwitterionic headgroups. We compare their physicochemical properties, their performance in in vitro and in vivo pharmacokinetic models, and their efficacy in peripheral lymphocyte lowering. The campaign resulted in the identification of several potent S1P1 receptor agonists with good selectivity vs S1P3 receptors, efficacy at 1 mg/kg oral doses, and developability properties suitable for progression into preclinical development.

Discovery of a selective S1P1 receptor agonist efficacious at low oral dose and devoid of effects on heart rate

Gilenya (fingolimod, FTY720) was recently approved by the U.S. FDA for the treatment of patients with remitting relapsing multiple sclerosis (RRMS). It is a potent agonist of four of the five sphingosine 1-phosphate (S1P) G-protein-coupled receptors (S1P1 and S1P3-5). It has been postulated that fingolimod's efficacy is due to S1P1 agonism, while its cardiovascular side effects (transient bradycardia and hypertension) are due to S1P3 agonism. We have discovered a series of selective S1P 1 agonists, which includes 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy] phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl] propanoate, 20, a potent, S1P3-sparing, orally active S1P1 agonist. Compound 20 is as efficacious as fingolimod in a collagen-induced arthritis model and shows excellent pharmacokinetic properties preclinically. Importantly, the selectivity of 20 against S1P3 is responsible for an absence of cardiovascular signal in telemetered rats, even at high dose levels.

Pyridin-3-yl derivatives as immunomodulating agents

The invention relates to pyridin-3-yl derivatives of Formula (I) wherein R1, R2, R3, R4, R5; R6 and A are as described in the description, their preparation and their use as pharmaceuticall